98902-17-1

Upstream product

• 23873-66-7 N-methyl-N-cyanoethyl benzamide 
• 65-85-0 benzoic acid 
• 109-81-9 N-methyl-ethane-1,2-diamine 
• 93-58-3 benzoic acid methyl ester 
• 6291-84-5 N-Methyl-1,3-propanediamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 65189-49-3 N-{3-[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-propyl}-benzamide; hydrochloride 

Relevant academic research and scientific papers

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines

Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.

Selective benzoylation of primary amines in the presence of secondary amines

Compounds containing both primary and secondary amine moieties in the same molecule were treated sequentially with two equivalents of n-butyllithium at room temperature, two equivalents of TMSCI, one equivalent of n-butyllithium and one equivalent of benzoyl chloride, to afford mono-benzoylated diamines. Under these conditions, the primary amine moiety was selectively benzoylated.

Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives

A series of N2-[(acylamino)alkyl]-6,7-dimethoxy-2,4-quinazolinediamines was synthesized as potential α1-adrenoceptor antagonists. When administered to spontaneously hypertensive rats at 10 mg/kg po, a number of propanediamine derivatives showed good antihypertensive activity, whereas the ethanediamine derivatives, albeit being structurally more closely related to prazosin, were devoid of this property. The most active derivative, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro- 2-furancarboxamide hydrochloride, alfuzosin, showed high selectivity for peripheral α1-postjunctional adrenoceptors. At equiactive antihypertensive doses, its effect on the pressor response to postural changes in conscious dog was less marked than that shown by prazosin. In the light of these results, alfuzosin was selected for clinical evaluation.